Understanding the Entrepreneurial Cliff

On November 21, 1983, Hjallis “Harry” Harkimo found himself 10 feet below his boat in the middle of a stormy, pitch-black night in the Indian Ocean 200 miles from land. Harry was on the South Africa-to-India leg of the Whitbread Round the World Solo Sailing Race when a wave capsized his boat just after 3 a.m. He spent the next two hours fighting for survival—and, even though it was the last thing likely to be on his mind at the time, building a foundation that would produce sustained entrepreneurial excellence for decades to come.

I met Harry in 1993 when I was tasked with creating an international hockey tournament in Helsinki, Finland. As VP of Business Development for the NHL at the time, I was eager to grow international television revenue and showcase the NHL’s rising young Finnish star, Teemu Selänne, in his hometown against Finnish pros. While I was searching for a local partner, five consecutive references gave me Harry’s number. Harry was the owner of Jokerit, the Finnish hockey equivalent of the New York Yankees, and everyone knew that Harry would be the perfect partner for the NHL in Finland. They were right. I quickly learned that Harry was kova jätkä—Finnish for “badass.”

Upon reaching an agreement on a deal to partner on the NHL International Challenge with the NHL’s Winnipeg Jets and Finnish hockey teams Jokerit, Tampere and HIFK, we went to dinner to celebrate. I soon came to understand that 90 percent of Finland knew Harry, and most seemed to know him personally. He would park his car, banter and laugh easily with the attendant before going to a meeting with the CEO of Finland’s largest broadcaster and diving into a similar conversation. The conversations were in Finnish, and the only thing I could discern was the zeal with which Harry approached each conversation and the authenticity of his counterpart’s reaction. Ninety percent of the hundreds of interactions on which I accompanied Harry over 10 months concluded with a hug.

Harry is respected throughout Finland and across European business circles as a smart, direct, resilient entrepreneur who has built successful companies across multiple disciplines. Solo sailing adventurer, businessman, sports team owner, TV star (he hosted the Finnish version of The Apprentice), elected member of the Finnish Parliament and more—Harry has done it all, done it well and left a strong impression on everyone he’s met. He traces it back to that hellish night in the Indian Ocean.

“What drives you, Harry? What fuels you?” I asked him over dinner recently.

“Each project is like a religious crusade,” he answered. “My job is to help people be part of something special, something they can’t ever forget when it is over.” The two hours he spent righting his boat and fighting for his life were transformative, he added.  “If I am going to lead that crusade, I have to believe that I can figure out whatever is placed in our path.”

Harry advocates taking yourself to the “edge of the cliff”—that stress-inducing experiences become easier when replicated, and that cross-pollination happens when those risks are taken across disciplines. Harry recalls feeling like he had superhuman strength and extreme clarity of purpose on his night in the Indian Ocean—the peril and stress of his situation focused him that profoundly. He doesn’t advocate recklessness and daredevil behavior—he just feels strongly that he needed to be pushed in this way to achieve and internalize a clarity of purpose that he now taps into every day. Harry swears that it was only achieved by what he calls “looking over the cliff”—in this case, facing death, and physically and mentally coming through it that much stronger and wiser.

“Everyone has their own cliffs—it is very personal,” he says. “It just seems that people who repeatedly lead effective entrepreneurial efforts understand what it means to look over cliffs and sustain. You learn first and foremost to control what you can control”—and learn to roll with what you can’t.

Harry suggested that it impacted those times later in life when he wasn’t sure—on multiple occasions—that he could make payroll in the next 24 hours, wasn’t sure if financing was going to fall into place days before ground breaking on a Helsinki ice arena he conceived and built and wasn’t sure on at least 20 occasions that his team could deliver promised results under unforeseen adverse circumstances.

To be clear, Harry has not always succeeded. His every move dissected and scrutinized by the entire nation, he has spent a lot of time in the Finnish tabloids, which is not easy or fun. Regardless, he goes about his daily business always with an eye out for his next adventure. His longtime friend, Teemu Selänne has watched Harry face down hundreds of challenges over their almost 30-year friendship.

“If I were given a near-impossible mission that I had to complete to, God forbid, save my family’s lives, and I could only choose one person to join me, Harry would be my choice,” Teemu told me on a recent call. Finland is home to just over 5.5 million people, and it is a sure bet that many of them would say the same.

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